Sodium Chloride → 1,3-Dibromo-5-(methylsulfanyl)benzene

HRID 653622ノート

反応式

HRID 653622 の反応式
C([Li])CCC.[Br:6][C:7]1[CH:12]=[C:11](Br)[CH:10]=[C:9]([Br:14])[CH:8]=1.[CH3:15][S:16]SC.[Cl-].[Na+]>CCOCC.O1CCCC1.C(OCC)(=O)C>[Br:6][C:7]1[CH:12]=[C:11]([S:16][CH3:15])[CH:10]=[C:9]([Br:14])[CH:8]=1

参加物

8

反応物 4

HCID 5234Sodium ChlorideHCID 12232Dimethyl DisulfideHCID 122791,3,5-TribromobenzeneHCID 178418339Butyllithium

生成物 1

HCID 190104071,3-Dibromo-5-(methylsulfanyl)benzene

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A 2.5M solution of n-butyllithium (42 mL; 0.105M) was added over 25 mins. to a vigorously stirred suspension of 1,3,5-tribromobenzene (31.5 G; 0.1M) in 1.6 L of anhydrous ether and 400 mL of anhydrous tetrahydrofuran under nitrogen at -78°. After stirring the mixture 30 minutes, 2 equivalents of dimethyldisulfide was added dropwise. The resulting mixture was stirred at R.T. overnight. 150 mL of sat'd sodium chloride solution was cautiously added. 500 mL of ethyl acetate was added. The organic phase was separated, and dried over anhyd. magnesium sulfate. Solvent removal gave a crude product, which was purified on silica gel using hexane as solvent. The desired product was isolated and distilled at 107°-110°/~1 mm to give 18 G of 3,5-dibromothioanisole as a colorless liquid, which slowly solidified on standing.

後処理

  1. additionwas added dropwise
  2. customThe organic phase was separated
  3. customdried over anhyd
  4. customSolvent removal
  5. customgave a crude product, which
  6. customwas purified on silica gel

出典と根拠

ORDレコード
ord-4124a0cc7c534584a11046d859077aba
出典データセット
uspto-grants-1992_07
特許番号
US05128335

反応ノート

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